1. Field of Invention
The present invention relates to water-soluble and water dispersible UV absorbing compounds and substantive anti-dandruff compounds and compositions thereof. The invention particularly relates to anti-dandruff and UV absorbing quaternary salts of Undecylenicamidoalkyl amine of Formula I,
wherein    R1, R2 are from C1-C6 carbon atoms,    R3 is undecylenic acid,    amino group selected from dimethyl amino propyl amine, which are substantive to skin, hair and fabric.
The present invention also relates to a process of preparation of these compounds and to the use of these compounds, in hair care, skincare & fabric care compositions.
2. Prior Art
It is known in art that many surfactants and additives used in shampoo products cause irritation to the eyes, which is of particular concern in shampoos used on infants and children. Accordingly attempts are made in prior art to develop surfactants and additives that are less irritating in nature.
It is observed that as children approach the age of puberty, hormonal changes associated with the development of scalp conditions normally associated with dandruff, such as scalp irritation and scaling, often occur. Incorporation of anti-dandruff agents thus becomes essential in hair care products for the treatment of the infected scalp.
For example, Undecylenic acid, which is commercially available, is used as an anti-dandruff agent in shampoos however it is a primary irritant and toxic substance.
Other known anti-dandruff molecules reported in Chemical products Desk reference compiled by Michael & Irene Ash.—that are based on Undecylenic acid are Undecylenamide DEA (CTFA) CAS # 25377-64-1; 60239-68-1, Undeylenamide MEA (CTFA) CAS # 20545-92-0; 25377-63-3, Undecylenamidopropyl trimonium methosufate, Undecylenic quat ammonium methosulfate, Undecylenic sulfosuccinate.
U.S. Pat. No. 4,307,089 discloses a cosmetic formulation consists of pyrithione compound in combination with undecylenic acid monoalkylolamide sulfosuccinate half ester for treatment of dandruff.
U.S. Pat. No. 3,385,755 discloses antibacterial and antifungal agents derived from Undecylenic acid alkylolamide and its derivative like undecylenic acid monoalkylolamide sulfosuccinate half ester.
U.S. Pat. No. 6,333,027 discloses a composition to treat dandruff in which Undecylenic amidopropyl betain is one of the active ingredients.
However these agents and compositions have found to be less effective against dandruff and there exists a need in the art to have a superior anti-dandruff agent that gives a long lasting protection against dandruff.
Other reported anti-dandruff products like ZPTO, Ketoconazole are either water-soluble or oil soluble. It is difficult to have clear shampoos with ZPTO and generally settling at the bottom is observed. Ketaconazole also requires additives for improving its solubility in formulations.
Therefore, there is a need for more effective anti-dandruff compounds, which has low degree of eye and skin irritation; effectively treat dandruff, and have superior physical characteristics that enable them to be easily formulated in hair care products.
The present inventors have surprisingly found that quaternary ammonium salts having two undecylenic acid moieties not only have more superior anti-dandruff activity compared to prior art compounds but also have dual water and oil solubility and are less irritant and are non-toxic.